Title: Woodbury Vacation Rentals from CA $165: Short-Term Rentals for 2026 | Expedia.ca

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![Madison Green Historic District with Landmark Buildings and Architecture in Madison Downtown, Connecticut, USA](https://images.trvl-media.com/place/176243/8b54eb68-713c-4dbe-aa0d-dadb147aaa07.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=176243&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=176243&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=176243&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=176243&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Woodbury vacation rentals

![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/07823851.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/fb67eeb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/c873cf3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/112000000/111830000/111828700/111828646/a51d4c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy One Bedroom Apartment Centrally Located in Southbury

[](https://www.expedia.ca/Southbury-Hotels-Simple-Living-Retreat-1-Bedroom-Apartment.h111828646.Hotel-Information)

Southbury

10/10

Exceptional

(22 reviews)

"Perfect sized apartment for a short stay - very convenient to my destination"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

S

CA $120

CA $165 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Southbury-Hotels-Simple-Living-Retreat-1-Bedroom-Apartment.h111828646.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112280000/112274100/112274050/1f47055b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112280000/112274100/112274050/c2f2be51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/113000000/112280000/112274100/112274050/5c375585.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/113000000/112280000/112274100/112274050/e71bf92b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Apartment in Southbury 103

[](https://www.expedia.ca/Southbury-Hotels-Private-Apt-In-Southford-Southbury.h112274050.Hotel-Information)

Southbury

10/10

Exceptional

(2 reviews)

"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dominick S.

CA $138

CA $371 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Southbury-Hotels-Private-Apt-In-Southford-Southbury.h112274050.Hotel-Information)

![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/0eb76bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/a1d7bab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/d9bfd1d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, Netflix, streaming services](https://images.trvl-media.com/lodging/96000000/95040000/95032200/95032165/446f217c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

[](https://www.expedia.ca/New-Haven-Hotels-Urban-Oasis-3BR-Parking-Washer-Dryer-Yale-East-Rock.h95032165.Hotel-Information)

East Rock

9.8/10

Exceptional

(11 reviews)

"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Denyce D.

CA $143

CA $382 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/New-Haven-Hotels-Urban-Oasis-3BR-Parking-Washer-Dryer-Yale-East-Rock.h95032165.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/eab09613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/970a479f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/ba8d6f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91310000/91304700/91304625/375323f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

[](https://www.expedia.ca/Torrington-Hotels-Cozy-3-Flr-Private-1-Bdrm-Apt-Tree-Line-View.h91304625.Hotel-Information)

Torrington

9.2/10

Wonderful

(5 reviews)

"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rhonda H.

CA $109

CA $453 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Torrington-Hotels-Cozy-3-Flr-Private-1-Bdrm-Apt-Tree-Line-View.h91304625.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/3db87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/979641d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/38f44943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/bf37a122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CT Gate House Goshen CT, Gate House Goshen CT

[](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information)

Goshen

9.4/10

Exceptional

(9 reviews)

"The property was great and the house was huge even for all 12 of us "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan L.

CA $129

CA $870 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/2db3f072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/646c7316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/bdac0629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/0888acaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All New 1BR with tons of Charm

[](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.Hotel-Information)

Wallingford Center

9.8/10

Exceptional

(8 reviews)

"Charming, unique, and very comfortable. Would surely stay again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David S.

CA $157

CA $396 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122400000/122391400/122391367/2372fa1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/123000000/122400000/122391400/122391367/0984b254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122400000/122391400/122391367/9d78d185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122400000/122391400/122391367/659e94b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

[](https://www.expedia.ca/Southington-Hotels-Welcoming-1500-Square-Foot-3-Bedroom-House-Completely-Remodeled-In-Southington.h122391367.Hotel-Information)

Southington

10/10

Exceptional

(2 reviews)

"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cindy M.

CA $134

CA $700 total

includes taxes & fees

Feb 14 - Feb 15

[](https://www.expedia.ca/Southington-Hotels-Welcoming-1500-Square-Foot-3-Bedroom-House-Completely-Remodeled-In-Southington.h122391367.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/62b2e5a8_edited_33e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/624102e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/efeecab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/a5ee2415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

[](https://www.expedia.ca/Cheshire-Hotels-Quiet-2-Bedroom-Apartment-In-Wonderful-Cheshire-With-WiFi-And-Beautiful-Views.h111824460.Hotel-Information)

Cheshire

9.4/10

Exceptional

(16 reviews)

"Needed a place to sleep for a couple of nights and this worked for us."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James (Jim) L.

CA $122

CA $230 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Cheshire-Hotels-Quiet-2-Bedroom-Apartment-In-Wonderful-Cheshire-With-WiFi-And-Beautiful-Views.h111824460.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/dad41f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/4b86b544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/ac508f02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/f2a274b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All New Studio apartment in center of town

[](https://www.expedia.ca/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.Hotel-Information)

Wallingford Center

10/10

Exceptional

(2 reviews)

"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nadine C.

CA $157

CA $396 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/9fd3ea2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/w4027h3019x0y0-7deed843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/d0920f95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/113000000/112999100/112999076/fc0e0fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  The Nest At Elm City Flats.

[](https://www.expedia.ca/New-Haven-Hotels-Overlook-New-Haven-In-This-2-BDR-Peaceful-Carribean-Nest.h112999076.Hotel-Information)

West New Haven

9.6/10

Exceptional

(7 reviews)

"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joan S.

CA $122

CA $322 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/New-Haven-Hotels-Overlook-New-Haven-In-This-2-BDR-Peaceful-Carribean-Nest.h112999076.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/996b1a71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/5f2a3ee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/0612bb56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110380000/110372000/110371901/c14b3372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Sun Filled Cozy Creamery

[](https://www.expedia.ca/Plainville-Hotels-The-Sun-Filled-Cozy-Creamery.h110371901.Hotel-Information)

Plainville

8.8/10

Excellent

(25 reviews)

"Very cozy and comfortable.The location was perfect for our stay in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Heather T.

CA $94

CA $346 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Plainville-Hotels-The-Sun-Filled-Cozy-Creamery.h110371901.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/453bb440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/acd6c55a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/86a2247f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100400000/100397900/100397846/b44a1a8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #31 - Downtown Terryville- 1 Br

[](https://www.expedia.ca/Terryville-Hotels-31-Downtown-Terryville-1-Br.h100397846.Hotel-Information)

Plymouth

10/10

Exceptional

(1 review)

"In convenient safe area. Os is easy to contact"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gina P.

CA $135

CA $328 total

includes taxes & fees

Feb 14 - Feb 15

[](https://www.expedia.ca/Terryville-Hotels-31-Downtown-Terryville-1-Br.h100397846.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/abc38fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/cc285c9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/90f4ffc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/96000000/95040000/95033700/95033642/w905h683x59y0-78a87dbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Angelica’s safe haven @ west haven

[](https://www.expedia.ca/West-Haven-Hotels-Angelicas-Safe-Haven-West-Haven.h95033642.Hotel-Information)

West Haven

10/10

Exceptional

(6 reviews)

"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Veronica

CA $178

CA $451 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/West-Haven-Hotels-Angelicas-Safe-Haven-West-Haven.h95033642.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/02904b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/9dab6fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/43b2916f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/a94b7e4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### One bedroom apartment in United States of America, New Haven

[](https://www.expedia.ca/New-Haven-Hotels-One-Bedroom-Apartment-In-United-States-Of-America.h120065513.Hotel-Information)

Dwight

8.6/10

Excellent

(4 reviews)

"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Philip S.

CA $130

CA $280 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/New-Haven-Hotels-One-Bedroom-Apartment-In-United-States-Of-America.h120065513.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/120000000/119680000/119675600/119675548/b2d32876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/120000000/119680000/119675600/119675548/b7b742fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119680000/119675600/119675548/fd7534e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119680000/119675600/119675548/c81037cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Two Bedroom Stay In Downtown New Haven!

[](https://www.expedia.ca/New-Haven-Hotels-Cozy-Two-Bedroom-Stay-In-Downtown-New-Haven.h119675548.Hotel-Information)

Dwight

10/10

Exceptional

(1 review)

"Exactly as advertised and had nice personal touches. Very close to attractions and very walkable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kimberly S.

CA $149

CA $374 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/New-Haven-Hotels-Cozy-Two-Bedroom-Stay-In-Downtown-New-Haven.h119675548.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92870000/92867400/92867391/4844e3ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92870000/92867400/92867391/2a815547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathtub, free toiletries, bathrobes, towels](https://images.trvl-media.com/lodging/93000000/92870000/92867400/92867391/3692a8cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/93000000/92870000/92867400/92867391/2e021907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Apartment in Southbury 101

[](https://www.expedia.ca/Southbury-Hotels-Private-Apt-In-SouthfordSouthbury-101.h92867391.Hotel-Information)

Southbury

9.4/10

Exceptional

(6 reviews)

"The apartment was nice, big area, loved this rental."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marissa G.

CA $145

CA $381 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Southbury-Hotels-Private-Apt-In-SouthfordSouthbury-101.h92867391.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/66000000/65400000/65395700/65395652/9bd3b6fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/66000000/65400000/65395700/65395652/cfcd4e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/66000000/65400000/65395700/65395652/4316e2bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/66000000/65400000/65395700/65395652/756b3f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly Remodeled with deck. Close to town center

[](https://www.expedia.ca/Wallingford-Hotels-Newly-Remodeled-With-Deck-Close-To-Town-Center.h65395652.Hotel-Information)

Wallingford

10/10

Exceptional

(2 reviews)

"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen F.

CA $157

CA $396 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Wallingford-Hotels-Newly-Remodeled-With-Deck-Close-To-Town-Center.h65395652.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/7ce55fe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/519bb10d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/97b3c47c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99480000/99476700/99476616/897c3b48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #26 Beautifully Renovated 2 BR Home

[](https://www.expedia.ca/Plainville-Hotels-26-Beautifully-Renovated-2-BR-Home.h99476616.Hotel-Information)

Plainville

10/10

Exceptional

(4 reviews)

"We thoroughly enjoyed our stay! The space was great for our family of 4\. Would recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

LaTanya W.

CA $190

CA $369 total

includes taxes & fees

Feb 13 - Feb 14

[](https://www.expedia.ca/Plainville-Hotels-26-Beautifully-Renovated-2-BR-Home.h99476616.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/4172866e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/e15142a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/6e1b5e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/27201c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

[](https://www.expedia.ca/Oakville-Hotels-Watertown-Home-W-Yard-1-Mi-To-Echo-Lake-Park.h108996700.Hotel-Information)

Oakville

CA $250

CA $639 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Oakville-Hotels-Watertown-Home-W-Yard-1-Mi-To-Echo-Lake-Park.h108996700.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/1366870a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/163d5bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/6a37565c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/a9bb69c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

[](https://www.expedia.ca/Charming.h111683284.Hotel-Information)

Shelton

9.0/10

Wonderful

(2 reviews)

"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alex C.

CA $164

CA $266 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Charming.h111683284.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-21&endDate=2026-02-22&regionId=176243&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Woodbury%2C+Connecticut%2C+United+States+of+America&regionId=176243&latLong=41.544546%2C-73.208991&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CABIN)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Woodbury%2C+Connecticut%2C+United+States+of+America&regionId=176243&latLong=41.544546%2C-73.208991&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Woodbury%2C+Connecticut%2C+United+States+of+America&regionId=176243&latLong=41.544546%2C-73.208991&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Woodbury%2C+Connecticut%2C+United+States+of+America&regionId=176243&latLong=41.544546%2C-73.208991&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Woodbury%2C+Connecticut%2C+United+States+of+America&regionId=176243&latLong=41.544546%2C-73.208991&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Woodbury%2C+Connecticut%2C+United+States+of+America&regionId=176243&latLong=41.544546%2C-73.208991&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VILLA)

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## Top Woodbury Hotel Reviews

![Hampton Inn Waterbury](https://images.trvl-media.com/lodging/2000000/1180000/1172400/1172343/757b15d7_y.jpg)

### Hampton Inn Waterbury

10/10 Excellent

"Everything was wonderful! The staff are amazing! I left my wedding ring and anniversary band and they found them and put them aside for me! I’m eternally grateful!!! "

[](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-Waterbury.h1172343.Hotel-Information)

![Ethan Allen Hotel](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/9fd70ba0_y.jpg)

### Ethan Allen Hotel

10/10 Excellent

"The room and building were clean. Location off the high way was really convenient and it was close to a huge mall. Several restaurants were only a five minute drive. The room itself was a double full bed suite and it was clean and spacious. One thing to note, no smart tvs which would’ve been nice, we were traveling with children and there were like 20 local boring channels/ no cartoons or movies. "

[](https://expedia.ca/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information)

![Hyatt House Shelton](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/0d731ede_y.jpg)

### Hyatt House Shelton

10/10 Excellent

"Great "

[](https://expedia.ca/New-Haven-Hotels-HYATT-House-Shelton.h3482162.Hotel-Information)

![Hotel Zero Degrees Danbury](https://images.trvl-media.com/lodging/17000000/16270000/16263900/16263812/1fb60e7f_y.jpg)

### Hotel Zero Degrees Danbury

10/10 Excellent

"The property is well kept up. The front desk staff was helpful and very friendly! This is the best hotel spot in Danbury! I will be returning!"

[](https://expedia.ca/Danbury-Hotels-Hotel-Zero-Degrees-Danbury.h16263812.Hotel-Information)

![Holiday Inn Cheshire - Southington by IHG](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287_y.jpg)

### Holiday Inn Cheshire - Southington by IHG

10/10 Excellent

"Was clean"

[](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information)

![Hilton Garden Inn Shelton](https://images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg)

### Hilton Garden Inn Shelton

10/10 Excellent

"nice"

[](https://expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.Hotel-Information)

![Courtyard by Marriott Waterbury Downtown](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8_y.jpg)

### Courtyard by Marriott Waterbury Downtown

10/10 Excellent

"All of the above "

[](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information)

![The Blake Hotel](https://images.trvl-media.com/lodging/33000000/32130000/32129700/32129620/95723c61_y.jpg)

### The Blake Hotel

10/10 Excellent

"The suite was very spacious with kitchenette and dining table, and it's clean and modern. The entire staff was very friendly and helpful, from the front desk to valet! It's very close to everywhere at Yale University. "

[](https://expedia.ca/New-Haven-Hotels-The-Blake-Hotel.h32129620.Hotel-Information)

![Wyndham Southbury](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155_y.jpg)

### Wyndham Southbury

10/10 Excellent

"Room very clean, staff was friendly and professional "

[](https://expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.Hotel-Information)

## Find out more about Woodbury

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Woodbury. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Woodbury ](https://expedia.ca/Woodbury-Private-Vacation-Homes.d176243-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Woodbury ](https://expedia.ca/Woodbury-Apartments.d176243-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Woodbury ](https://expedia.ca/Woodbury-Cottages.d176243-aaCottages.Travel-Guide-Accommodation)
- [Motels in Woodbury ](https://expedia.ca/Woodbury-Motels.d176243-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Woodbury ](https://expedia.ca/Woodbury-Cabins.d176243-aaCabins.Travel-Guide-Accommodation)
- [Guest Houses in Woodbury ](https://expedia.ca/Woodbury-Guest-Houses.d176243-aaGuestHouses.Travel-Guide-Accommodation)
- [Farmstay in Woodbury ](https://expedia.ca/Woodbury-Agritourism.d176243-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Woodbury ](https://expedia.ca/Woodbury-Bed-And-Breakfast.d176243-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Villas in Woodbury ](https://expedia.ca/Woodbury-Villas.d176243-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Woodbury ](https://expedia.ca/Woodbury-Condos.d176243-aaCondos.Travel-Guide-Accommodation)
- [Lodges in Woodbury ](https://expedia.ca/Woodbury-Lodges.d176243-aaLodges.Travel-Guide-Accommodation)
- [Resorts in Woodbury ](https://expedia.ca/Woodbury-Resort-Hotels.d176243-aaResortHotels.Travel-Guide-Accommodation)
- [Inns in Woodbury ](https://expedia.ca/Woodbury-Inns.d176243-aaInns.Travel-Guide-Accommodation)

## Frequently asked questions

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